Oxidation of unsaturated aliphatic and arylalkyl alcohols by peroxydisulphate. Intramolecular cyclization of alkoxyl radicals

Abstract

Oxidation of unsaturated aliphatic and arylalkyl alcohols by the sodium peroxydisulphate–silver salt system has been studied. Both classes of alcohols lead to cyclic ethers through different pathways. The ratio of five- to six-membered cyclic ethers was established reliably by trapping the corresponding cyclic radicals with heteroaromatic bases. Since a general preference for the formation of the five-membered ring was observed, comparison has been made with other oxidizing systems. The products obtained are also interesting from the synthetic point of view.